CA2090770A1 - Process for the Preparation of Alcohols or Amines - Google Patents

Process for the Preparation of Alcohols or Amines

Info

Publication number
CA2090770A1
CA2090770A1 CA2090770A CA2090770A CA2090770A1 CA 2090770 A1 CA2090770 A1 CA 2090770A1 CA 2090770 A CA2090770 A CA 2090770A CA 2090770 A CA2090770 A CA 2090770A CA 2090770 A1 CA2090770 A1 CA 2090770A1
Authority
CA
Canada
Prior art keywords
weight
parts
amines
alcohols
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA2090770A
Other languages
French (fr)
Other versions
CA2090770C (en
Inventor
Gerhardt Horn
Carl D. Frohning
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Johnson Matthey PLC
Original Assignee
Hoechst AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6453173&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2090770(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of CA2090770A1 publication Critical patent/CA2090770A1/en
Application granted granted Critical
Publication of CA2090770C publication Critical patent/CA2090770C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • FMECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F25REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
    • F25BREFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
    • F25B43/00Arrangements for separating or purifying gases or liquids; Arrangements for vaporising the residuum of liquid refrigerant, e.g. by heat
    • F25B43/04Arrangements for separating or purifying gases or liquids; Arrangements for vaporising the residuum of liquid refrigerant, e.g. by heat for withdrawing non-condensible gases
    • F25B43/043Arrangements for separating or purifying gases or liquids; Arrangements for vaporising the residuum of liquid refrigerant, e.g. by heat for withdrawing non-condensible gases for compression type systems
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02Impregnation, coating or precipitation
    • B01J37/03Precipitation; Co-precipitation
    • B01J37/031Precipitation
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/80Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00Catalysts, in general, characterised by their form or physical properties
    • B01J35/30Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B01J35/391Physical properties of the active metal ingredient
    • B01J35/392Metal surface area
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/48Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/177Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of a carboxy group
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00Catalysts, in general, characterised by their form or physical properties
    • B01J35/60Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61Surface area
    • B01J35/61310-100 m2/g
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00Catalysts, in general, characterised by their form or physical properties
    • B01J35/60Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61Surface area
    • B01J35/615100-500 m2/g

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Power Engineering (AREA)
  • Analytical Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Mechanical Engineering (AREA)
  • Thermal Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The present invention relates to a process for the preparation of alcohols or amines by reaction of esters, fatty acids or nitriles with hydrogen at elevated temperature and pressure by means of a catalyst which, per 100 parts by weight of CuO, comprises 40 to 130 parts by weight of ZnO, 2 to 50 parts by weight of Al2O3 and optionally 0.5 to 8 parts by weight of oxide of Mn, Mo, V, Zr and/or alkaline earth metal, has a BET total area of 80 to 175 m2 per gram of catalyst in the non-reduced state, 75 to 95% of the BET total area being formed by pores having a radius rp ~ 15 nm.
CA002090770A 1992-03-04 1993-02-25 Process for the preparation of alcohols or amines Expired - Fee Related CA2090770C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4206750A DE4206750A1 (en) 1992-03-04 1992-03-04 METHOD FOR PRODUCING ALCOHOLS OR AMINES
DEP4206750.2 1992-03-04

Publications (2)

Publication Number Publication Date
CA2090770A1 true CA2090770A1 (en) 1993-09-05
CA2090770C CA2090770C (en) 1999-06-29

Family

ID=6453173

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002090770A Expired - Fee Related CA2090770C (en) 1992-03-04 1993-02-25 Process for the preparation of alcohols or amines

Country Status (11)

Country Link
US (2) US5550297A (en)
EP (1) EP0559053B2 (en)
JP (1) JP2721633B2 (en)
KR (2) KR100283706B1 (en)
CN (1) CN1040743C (en)
CA (1) CA2090770C (en)
DE (2) DE4206750A1 (en)
ES (1) ES2103039T5 (en)
MX (1) MX9301052A (en)
MY (1) MY109406A (en)
SG (1) SG44835A1 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY129140A (en) * 1994-11-07 2007-03-30 Shell Int Research Process and a catalyst for the direct hydrogenation of carboxylic esters
KR100457066B1 (en) 2002-04-22 2004-11-12 애경유화 주식회사 Hydrogenation catalysts, preparation thereof, and method for the preparation of gamma-butyrolactone from maleic anhydride using the catalyst
BR112014022814B1 (en) * 2012-03-13 2020-10-27 Benefuel Inc. production method of alkyl ester of fatty acids
DE102014013530A1 (en) 2014-09-12 2016-03-17 Clariant International Ltd. Extruded Cu-Al-Mn hydrogenation catalyst
CN107635660A (en) * 2015-03-26 2018-01-26 巴斯夫公司 Hydrogenolysis catalyst with peracid tolerance
GB201905293D0 (en) * 2019-04-15 2019-05-29 Johnson Matthey Plc Copper-containing catalysts

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51106528A (en) * 1975-03-15 1976-09-21 Kitaro Matsuki Gorufukurabuno hetsudo
US4283581A (en) * 1978-02-24 1981-08-11 Chevron Research Company Hydrogenation process
US4199479A (en) 1978-02-24 1980-04-22 Chevron Research Company Hydrogenation catalyst
IT1190783B (en) * 1981-04-29 1988-02-24 Davy Mckee Oil & Chem PROCESS FOR HYDROGENOLYSIS OF ESTERS OF CARBOXYLIC ACIDS
US5004845A (en) * 1981-08-20 1991-04-02 Davy Mckee (London) Limited Hydrogenation of aldehydes
DE3317725A1 (en) 1983-05-16 1984-11-22 Süd-Chemie AG, 8000 München CATALYST FOR METHANOL SYNTHESIS
EP0175558A1 (en) * 1984-09-17 1986-03-26 EASTMAN KODAK COMPANY (a New Jersey corporation) Process for the vapor phase hydrogenation of carboxylic acids to esters and alcohols
CA2026275C (en) * 1989-10-17 2000-12-05 Deepak S. Thakur Hydrogenation catalyst, process for preparing and process of using said catalyst
US5008235A (en) * 1989-12-21 1991-04-16 Union Carbide Chemicals And Plastics Technology Corporation Catalysts of Cu-Al-third metal for hydrogenation

Also Published As

Publication number Publication date
US5550297A (en) 1996-08-27
CN1040743C (en) 1998-11-18
DE4206750A1 (en) 1993-09-09
ES2103039T5 (en) 2006-06-01
KR100283975B1 (en) 2001-02-15
EP0559053A3 (en) 1994-04-13
KR930019596A (en) 1993-10-18
EP0559053B1 (en) 1997-05-07
CN1076438A (en) 1993-09-22
JPH069452A (en) 1994-01-18
MX9301052A (en) 1993-09-01
MY109406A (en) 1997-01-31
CA2090770C (en) 1999-06-29
ES2103039T3 (en) 1997-08-16
US5663445A (en) 1997-09-02
KR100283706B1 (en) 2001-04-02
EP0559053A2 (en) 1993-09-08
EP0559053B2 (en) 2005-12-14
SG44835A1 (en) 1997-12-19
DE59306359D1 (en) 1997-06-12
JP2721633B2 (en) 1998-03-04

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Legal Events

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